1. Field of the Invention
This invention relates to a method for inhibiting polymerization of maleimides. More particularly, it relates to a method for inhibiting polymerization of maleimides by using as a polymerization inhibitor at least one compound selected from the group consisting of thiodipropionic esters, 4-t-butyl-catechol, 2,4-dimethyl-6-t-butyl phenol, 2,5-di-t-butyl-hydroquinone, 2-t-butyl-hydroquinone, 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-1,3,5-triazine, 2,2'-thiobis-(4-methyl-6-t-butylphenol), 4,4'-thiobis-(6-t-butyl-m-cresol), and triethyleneglycol-bis-[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate]. It provides a method for conspicuously inhibiting polymerization of maleimides by the use of this specific polymerization inhibitor as during the production of maleimides from maleic anhydride and amines, during the purification of crude maleimides as by distillation, for example, or during the storage or transportation of maleimides, for example.
2. Description of the Prior Art
Maleimides, because of their molecular structures, are extremely unstable compounds which readily undergo polymerization. For this reason, various methods have been heretofore proposed for inhibiting polymerization of maleimides as during the production of maleimides from maleic anhydride and amines or during the purification of crude maleimides by distillation, for example. For the purpose of inhibiting polymerization of maleimides during the production or reaction of maleimides, for example, a method which causes a maleimide produced by the heat treatment of maleinamic acid under a vacuum to be quickly expelled by distillation from the reaction system is disclosed in the Japanese Patent Laid-Open No. SHO 47(1972)-27,974. In the Japanese Patent Laid-Open No. SHO 53(1978)-137,956, there is disclosed a method which produces a maleimide by preparatorily adding a hydrogen halide to the double bond of maleic anhydride as a raw material thereby depriving the double bond of polymerization reactivity and then allowing the maleic anhydride to react with an amine thereby effecting ring closing by dehydration. Neither of these patent publications teaches a method for inhibiting polymerization of maleimides and therefore permitting production of maleimides in satisfactorily high yields.
Further, methods which effect purification of crude maleimides while keeping the crude meleimides from exposure to heat as much as possible have been disclosed. In the Japanese Patent Laid-Open Nos. SHO 58(1983)-96,066 and SHO 60(1985)-100,554, for example, there are disclosed methods which effect the purification by recrystallizing the crude maleimides from such solvents as methanol, toluene, or isopropanol at relatively low temperatures.
Even when maleimides are purified under such conditions as described above, polymerization proceeds on the maleimides while the maleimides are held in storage. As the result, the maleimides will be deprived of their commercial value during the course of their storage.
In the case of a maleimide which contains therein the homopolymer of the maleimide, for example, when this maleimide is copolymerized with styrene or with styrene and acrylonitrile, the produced copolymer inevitably contains therein the homopolymer of the maleimide and, therefore, fails to acquire as high improved thermal stability and strength as expected. Further because the homopolymer of maleimide is insoluble in the comonomer, the copolymer is seriously impaired in appearance and transparency in particular and suffers from a heavy decline of commercial value.
It has been known to the art add (2,6-di-tert -butyl p-cresol) as a polymerization inhibitor to maleimides (British Patent No. 1,041,027). This compound has a disadvantage that while it manifests its effect sufficiently at low temperatures, it fails to manifest the effect sufficiently when it is heated to a high temperature.
As described above, it is very important to inhibit polymerization of maleimides as during the courses of production, purification, storage, and transportation. In spite of this importance, virtually no method has yet been proposed for effective inhibition of the polymerization of maleimides.
An object of this invention, therefore, is to provide a method for inhibiting polymerization of maleimides.
Another object of this invention is to provide a method for effectively inhibiting polymerization of maleimides without coloring maleimides.
Yet another object of this invention is to provide maleimide compositions which are prevented from coloration and polymerization.